Method for producing 16-dehydropregnenolone acetate

A technology of dienool ketone acetate and production method, applied in the directions of steroids, organic chemistry, etc., can solve the problems such as unrecoverable catalyst, complicated production process, increased cost, etc., so as to improve the utilization rate of raw materials and the yield of products. , the effect of reducing equipment requirements

Inactive Publication Date: 2014-09-17
CHENGDU LAURELSCI TECH
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  • Abstract
  • Description
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Problems solved by technology

[0005] (1) The catalyst cannot be recycled, which not only increases the cost but also pollutes the environment
[0006] (2) After the oxidation reaction, it is necessary to add an equivalent amount of reducing agent to remove the oxidizing agent, which makes the production process complicated
[0007] (3) The formation of by-products cannot be avoided

Method used

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  • Method for producing 16-dehydropregnenolone acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Take 4g of diosgenin and place it in a 100ml three-necked reaction flask, add 30ml of acetic anhydride and 18ml of glacial acetic acid, heat and stir on the electric heating mantle to dissolve, continue heating and reflux for 2h, stop heating, cool to room temperature, and obtain 52.4g of ring-opening reaction solution.

[0031] Put 52.4g of the ring-opening reaction solution into the bubbler, place the bubbler in an ice-water bath at about 10°C, and then pass in ozone, and continue the reaction for 1 hour. TLC will track the reaction until it is completely oxidized, and stop the introduction of ozone. The ozone is adsorbed by activated carbon, and 48.3 g of the oxidation reaction solution is taken out.

[0032] Add 20ml of water to 48.3g of the oxidation reaction solution, heat to 95°C and stir under reflux for 1.5h for hydrolysis, then distill the hydrolyzed solution to recover glacial acetic acid, then add 100ml of cyclohexane and petroleum ether to the still liquid (...

Embodiment 2

[0034] Take 35g of diosgenin and place it in a 1000ml three-necked reaction bottle, add 400ml of acetic anhydride and 80ml of glacial acetic acid, heat and stir on the electric heating mantle to dissolve, continue to heat and reflux for 1.5h, stop heating, cool to room temperature, and obtain 443.6g of ring-opening reaction solution .

[0035] Pass 443.6g of the ring-opening reaction liquid into the bubbler, place the bubbler in an ice-water bath at about -5°C, and then pass through ozone, and continue the reaction for 2.5 hours. TLC will track the reaction until it is completely oxidized, and then stop the introduction of ozone , excess ozone was adsorbed with active carbon, and 385.7 g of the oxidation reaction solution was taken out.

[0036] Add 200ml of water to 385.7g of the oxidation reaction solution, heat to 95°C and stir to reflux for 2 hours for hydrolysis, then distill the hydrolyzed solution to recover glacial acetic acid, then add 1000ml of cyclohexane to the sti...

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Abstract

The invention discloses a method for producing 16-dehydropregnenolone acetate. The method comprises the following steps: carrying out ring opening on diosgenine as a raw material, oxidizing, hydrolyzing, and refining to produce highly 16-dehydropregnenolone acetate. Compared with traditional 16-dehydropregnenolone acetate production methods, the method especially adopting highly active ozone as an oxidant in the oxidation reaction process has the advantages of novelty, mild reaction conditions, and easy control of the reaction product; the total yield of separated 16-dehydropregnenolone acetate reaches 79.5%, and is higher than an industrial average production level of 72-74%; and the oxidant in the reaction process can be recycled, so the method also has the advantages of realization of continuous production, production cost reduction, investment saving, labor intensity mitigation, high comprehensive utilization rate, and environmental protection, and provides a reference for the industrial production.

Description

technical field [0001] The invention belongs to the technical field of production of steroid hormone intermediates, and in particular relates to a production method of high-purity dienolone acetate. Background technique [0002] The chemical name of dienolone acetate (referred to as diene) is: 5,16-pregnadiene-3β-ol-20-one acetate, and the molecular formula is C 23 h 32 o 3 . It is an important intermediate for the synthesis of steroid hormone APIs, and it can be used as a raw material to produce adrenal hormone drugs (such as hydrocortisone, hydroprednisone), glucocorticoid drugs, and steroidal anti-inflammatory drugs (such as Dexamethasone acetate, fluocinolone) and sex hormone drugs (such as progesterone) and female oral contraceptives, etc. At present, the industrial production of dienolone acetate is mainly semi-synthesized from steroids isolated from natural resources. The main raw materials for the synthesis of dienolone acetate are solanite, diosgenin, sisal sap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
Inventor 文静蒋宇王宇璐曾蓉
Owner CHENGDU LAURELSCI TECH
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